Annual Cookie Day for the Christmas Season

The O’Halloran Family Cookie Day

  • 1,000+ sprinkles on the floor
  • 56 sticks of butter
  • 30 batches of cookies
  • 24 bakers and helpers
  • 9 different kinds of cookies
  • 1 special tradition

Ever since I can remember, we’ve held cookie day in my mom’s kitchen right before the holidays. When we were younger, that meant my brothers and I could each invite a friend or two over, and we would spend the day baking and decorating with my mom.  Sweet smells would fill the house and each friend would leave with a plate full of cookies piled high!  My brothers and I would make cookie plates for all of the neighbors, and take turns ringing the doorbells on our deliveries.

Some years, my grandma, Meme would come all the way from Missouri to help.

Some years we wore ugly sweaters, ugly aprons, and even one time a bunny pajama ensemble. Looking good Bridge…


As the years passed…cookie day evolved into a big PARTY. Instead of 1 friend, we were each having 3-4 over for the big day!

Yes, cookies were baked. Cookies were decorated. and gosh darn it, cookies were eaten! But it transformed into a day focused more on friendship, laughter, and getting together around the holidays.

Now, all of the “kids” are adults. And instead of drinking hot chocolate…we’re drinking sangria and beer!

My mom, being the overachiever that she is, bakes 20 batches of cookies beforehand just to prep for the big day. Yep, you heard that right. Twenty! Starting after Thanksgiving, she starts whipping out a few batches each night and then freezes them. Her freezer can’t hold all of the cookies…so she enlists the help of neighbors and friends and uses their freezer space too! Pretty crazy right?

Then the big day comes. Everyone arrives around noon and we start getting to work!
My mom delegates responsibilities.

Rolling dough.

Mixing up the batter.

And the best job of all…decorating!


Somehow there are always enough jobs for the 20+ “cooks” in the kitchen.

Without a doubt, something always goes wrong! Cookies burn, baking soda is forgotten in a recipe, or we run out of sprinkles! 

 But in the end it always works out.

It turns into a magical day that people of all ages enjoy!


After the final cookie is decorated…it is then time to make the big cookie plates!

Personally, this is my favorite part. Everyone creates a big plate to bring home, and grabs a handful of each of the 9 different types of cookies.  You load up your favorites. For me, that means the coconut krispies and peanut butter Reese’s cookies), until all of the cookies are gone!


My mom says I will soon “inherit” cookie day and give her a much needed break.  No more late night baking and messy kitchens for her! She certainly has been a trooper all these years, and I admit it probably is time for her to pass the torch to me. 

That means I should probably start preparing now for Cookie Day 2013!



The Year of Casey

Hey there!

I’m Casey Finn, the voice behind The DIY Playbook. I’m married to Finn & mom to Rory and Ellis. Together we’re creating our dream home in Chicago, one DIY project at a time.